'We Had This Massive Connection': What John Cusack's Exes Have Said About Him

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John Cusack prefers to keep his relationships to himself. Cusack remains one of the rare celebs who never got married, and rarely discusses his love life. Interestingly, the women he has been linked to over the years have adopted a similar approach. Some of his previous romantic partners have offered up some comments about what they think of Cusack, however, and none of it's been bad. The first to discuss her relationship with the "Being John Malkovich" actor was Melissa Gilbert.

In her 2009 memoir "Prairie Tale," Gilbert noted she was in relationship with Rob Lowe when she became involved with Cusack, Lowe's co-star in the 1983 film, "Class." "We ended up having a little fling, which I kept from Rob ... He was very sweet — and funny," Gilbert wrote. Years later, another girlfriend he had in the '80s opened up. In a 2013 interview, Susannah Melvoin, who was once Prince's backup singer and dancer, shared a similar opinion of her ex. "John Cusack is very funny and smart," she told Dyes Got the Answers 2 Ur ?s.

More recently, Minnie Driver, who is rumored to have dated Cusack around the time they filmed the 1997 film "Grosse Pointe Blank," admitted they clicked right away. "We had this massive connection," she said on "This Life of Mine... with James Corden" in 2024. She praised him again in 2026. "[He's] incredibly intellectually challenging and stimulating and fun," she told E! Live (via People). While Gilbert, Melvoin, and Driver have spoken highly of Cusack, they kept the details of their relationship to themselves. His "Say Anything" co-star, Ione Skye, however, didn't hold back all she hadto say.

Most of the women John Cusack has been with have said little or nothing about their time together. But his "Say Anything" co-star, Ione Skye, actually gave pretty decent insight into what was going on in his private life around the time they filmed their massive 1989 hit. While discussing the plot of the film, Skye asked him about his love life. He replied: "I've never been in love. At least not till recently," she recalled in her 2025 memoir, "Say Everything" (via Entertainment Tonight).

His remarks made her wonder whether or not their onscreen chemistry was pouring into their real-life relationship, which was just platonic at the time. But she quickly later learned Cusack was actually referring to his then-girlfriend, Susannah Melvoin. And thus, they continued to act out their chemistry onscreen only — at least back then. After Skye divorced Beastie Boys' Adam Horovitz in 2000, she reconnected with her former co-star. "I'd needed to get him out of my system and it had worked — now I knew we were meant to be in love only in the movies," she revealed.

Cusack was reportedly hurt by Skye's depiction of their romance. "You made the experience sound so meh! It wasn't 'meh' for me," she recalled him texting her in a 2025 interview with People. But she stood by her depiction. "It was more about how all of our chemistry was in our working together and stimulating each other's minds, not sleeping together!" Skye said, adding, "I felt a little bad, but, oh well." Cusack might have never married, but it sounds like he was a pretty decent romantic partner.